Title: Winter Park Cottages from CA $198 | Expedia.ca [Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.ca/Winter-Park.d7902.Destination-Travel-Guides) ![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Park cottages ![Exterior](https://images.trvl-media.com/lodging/92000000/91660000/91651500/91651407/38175f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91660000/91651500/91651407/43851998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91660000/91651500/91651407/bd0116b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/92000000/91660000/91651500/91651407/1f50c5c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lake Mary Guest House • Warm, Cozy & Inviting [](https://www.expedia.ca/Lake-Mary-Hotels-Orlando-Springs-Break-Cottage-With-Pool.h91651407.Hotel-Information) Lake Mary 9.8/10 Exceptional (48 reviews) "Absolutely perfect location! It was truly one of the best places we have stayed at!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaelyn M. CA $171 CA $388 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Lake-Mary-Hotels-Orlando-Springs-Break-Cottage-With-Pool.h91651407.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/ae67c445.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/21a7018d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/9e07e949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/111000000/110820000/110816000/110815947/cfe5ad56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown Cottage [](https://www.expedia.ca/Orlando-Hotels-Downtown-Cottage.h110815947.Hotel-Information) Colonialtown North 8.6/10 Excellent (8 reviews) "Clean perfect location for what we needed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerred B. CA $74 CA $226 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-Downtown-Cottage.h110815947.Hotel-Information) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/0104505e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/03c563d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/96a79e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537200/93537181/b54d3a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deltona Lake House, Day Trip to Disney & Universal [](https://www.expedia.ca/Deltona-Hotels-Home-On-Lake.h93537181.Hotel-Information) Deltona Lakes 10/10 Exceptional (3 reviews) "This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $186 CA $463 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Deltona-Hotels-Home-On-Lake.h93537181.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/bd3338e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/bbd3365c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/95ab5ded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/89000000/88630000/88627200/88627180/0ba4a661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Hidden Cottage [](https://www.expedia.ca/Orlando-Hotels-Tiny-Cottage.h88627180.Hotel-Information) Longwood 9.4/10 Exceptional (63 reviews) "Great little cottage, it was easy to locate and access the property. Nice quiet area and we really enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anna M. CA $97 CA $198 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Orlando-Hotels-Tiny-Cottage.h88627180.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95920000/95910800/95910740/ea89a698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95920000/95910800/95910740/f31b883a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95920000/95910800/95910740/5a4de37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games](https://images.trvl-media.com/lodging/96000000/95920000/95910800/95910740/94e9e749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweetheart Cottage Near Downtown Lake Mary•Queen Bed, Fire Pit & Private Lanai [](https://www.expedia.ca/Lake-Mary-Hotels-Cozy-Cottage-With-Queen-Bed-Private-Lanai-Lake-Mary.h95910740.Hotel-Information) Lake Mary 10/10 Exceptional (18 reviews) "An excellent location for stays in Lake Mary. It has everything a single or a couple needs to feel at home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kanzeda C. CA $144 CA $355 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Lake-Mary-Hotels-Cozy-Cottage-With-Queen-Bed-Private-Lanai-Lake-Mary.h95910740.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/w2408h1170x62y0-7347922c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/5d9eae4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/713a32e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/38000000/37150000/37148700/37148655/54993cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Incredible Private Lakefront Cottage Retreat [](https://www.expedia.ca/Orlando-Hotels-Private-Lakefront-Cottage.h37148655.Hotel-Information) Altamonte Springs 10/10 Exceptional (31 reviews) "The host was great! Love the lake and building a fire!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebekah W. CA $176 CA $470 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Orlando-Hotels-Private-Lakefront-Cottage.h37148655.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/cd9f46f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/407b03dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/383ca7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/97000000/96030000/96021500/96021481/0a16e2ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway! [](https://www.expedia.ca/Orlando-Hotels-The-Coach-House-Entire-Home-2-Bedroom3-Bath-Orlando-Getaway.h96021481.Hotel-Information) College Park 9.8/10 Exceptional (33 reviews) "Absolutely beautiful place, fully equipped and close to everything. We very much enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara R. CA $277 CA $524 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Orlando-Hotels-The-Coach-House-Entire-Home-2-Bedroom3-Bath-Orlando-Getaway.h96021481.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472200/126472102/b97297ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472200/126472102/7d2cbd32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472200/126472102/0006fea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472200/126472102/96771c1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Jordan Boho Style Vacation Home [](https://www.expedia.ca/Orlando-Hotels-Red-Jordan-Boho-Style-Vacation-Home.h126472102.Hotel-Information) Meadow Woods CA $225 CA $611 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Orlando-Hotels-Red-Jordan-Boho-Style-Vacation-Home.h126472102.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122940000/122930800/122930746/07359b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/123000000/122940000/122930800/122930746/1bb03122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122940000/122930800/122930746/5cd56263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122940000/122930800/122930746/a33b9a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Romantic Lakefront Getaway with Balcony near Downtown Orlando [](https://www.expedia.ca/Orlando-Hotels-Romantic-Lakefront-Getaway-With-Balcony-Unit-A.h122930746.Hotel-Information) Orlando CA $142 CA $315 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-Romantic-Lakefront-Getaway-With-Balcony-Unit-A.h122930746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115690000/115685500/115685439/ef7a4918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115690000/115685500/115685439/7e953fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115690000/115685500/115685439/2a37ee05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115690000/115685500/115685439/ab4af385.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny House in Kissimmee sleeps 4, only 20 minutes to Disney/Universal [](https://www.expedia.ca/Orlando-Hotels-Charming-1-Bedroom-Private-Cottage-Sleeps-4-In-Kissimmee-Access-To-Pool-And-Gym.h115685439.Hotel-Information) Kissimmee CA $131 CA $296 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Orlando-Hotels-Charming-1-Bedroom-Private-Cottage-Sleeps-4-In-Kissimmee-Access-To-Pool-And-Gym.h115685439.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/e00350a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/ecbaa983.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/bd6596dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113100000/113092500/113092482/729334cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema [](https://www.expedia.ca/Orlando-Hotels-4193-Paragraph-Drive.h113092482.Hotel-Information) Kissimmee CA $285 CA $1,218 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-4193-Paragraph-Drive.h113092482.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123590000/123584200/123584108/d5a175a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123590000/123584200/123584108/a7258f42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123590000/123584200/123584108/e764f6ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123590000/123584200/123584108/7993bbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio [](https://www.expedia.ca/Orlando-Hotels-Tranquil-Lakefront-Retreat-WPrivate-Patio-Unit-B.h123584108.Hotel-Information) Orlando CA $157 CA $336 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Orlando-Hotels-Tranquil-Lakefront-Retreat-WPrivate-Patio-Unit-B.h123584108.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537100/93537063/6e87aee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537100/93537063/04218c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537100/93537063/f16646a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93537100/93537063/48c2411c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Orlando Family Getaway w/ Fenced Yard! [](https://www.expedia.ca/Orlando-Hotels-Chic-Orlando-Family-Getaway-W-Fenced-Yard.h93537063.Hotel-Information) Rosemont 10/10 Exceptional (1 review) CA $208 CA $742 total includes taxes & fees Mar 12 - Mar 13 [](https://www.expedia.ca/Orlando-Hotels-Chic-Orlando-Family-Getaway-W-Fenced-Yard.h93537063.Hotel-Information) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/31d337d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/612598fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/260bf372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391558/b8c088ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fire Pit & Yard: Updated Winter Garden Home! [](https://www.expedia.ca/Winter-Garden-Hotels-Updated-Winter-Garden-Home-W-Yard-Fire-Pit.h99391558.Hotel-Information) Winter Garden CA $250 CA $696 total includes taxes & fees Apr 2 - Apr 3 [](https://www.expedia.ca/Winter-Garden-Hotels-Updated-Winter-Garden-Home-W-Yard-Fire-Pit.h99391558.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-18&endDate=2026-03-19®ionId=7902&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_7902) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APART_HOTEL) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CABIN) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=CHALET) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Winter+Park%2C+Florida%2C+United+States+of+America®ionId=7902&latLong=28.6%2C-81.339233&adults=2&startDate=2026-06-02&d1=2026-06-02&endDate=2026-06-05&d2=2026-06-05&lodging=HOUSE_BOAT) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Cottages.d7902-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Cottages.d7902-aaCottages.Travel-Guide-Accommodation) ## Top Winter Park Hotel Reviews ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/4ca8f177_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "The staff was welcoming! The room was very clean and spacious. Loved the balcony. I wish the parking wasn’t as expensive. That’s the only negative thing I could say. Would definitely stay again." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Universal's Cabana Bay Beach Resort](https://images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 8/10 Good "The staff were great. Pool and lazy river looked nice but it was too cold when we were there." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.Hotel-Information) ![Holiday Inn Resort Orlando Suites - Waterpark by IHG](https://images.trvl-media.com/lodging/1000000/290000/281700/281608/6cbf5753_y.jpg) ### Holiday Inn Resort Orlando Suites - Waterpark by IHG 10/10 Excellent "Isaiah was very helpful " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Orlando-Suites-Waterpark.h281608.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/86e77c07_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 10/10 Excellent "Traveled with my family and we definitely had a great time! The staff was amazing and caring. The water park was fun my kids enjoyed it. " [](https://expedia.ca/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Room was very clean and staff was awesome. A nice little bar vibe in the lobby." [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/d062739a_y.jpg) ### Orlando International Drive North Hotel 4/10 Poor "The pool was opened and they had movies for kids in the evening. When we arrive at the hotel, at least the room was clean, but the water pressure to flush the toilets was terrible, the sink was also slow to drain and terrible. The room was to be cleaned every 3 days, but it was never cleaned. We had to ask for clean towels twice to be replaced. We had to empty out the garbage ourselves. The outside grounds by the parking lot Building B was always ditty, full of leaves and garbage the other people would throw out. Most of it was scattered on the floor, because the garbage bins were small and garbage was not picked up that often . They charged a resort fee which shouldn't even br charged. That location is not a resort. Breakfast was a goodie box with an egg sandwich, a pastry or an apple. Coffee and juice available at the cabana where they gave you the breakfast box. No coffee maker in the rooms either. The location of the hotel is the only good thing about it. This hotel needs to be updated and renovated. The cleaning crew hardly speak any English and it wa gard to even ask them for towel replacements and to throw out the garbage. It's sad but true. " [](https://expedia.ca/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information) ![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 4/10 Poor "One of the gentleman at the front desk was completed inacapable of handling any tasks. The other agents were lovely. Things were closed regularly from the Mini Bites store to the splash pad using caution tape. The bartender acted annoyed that we wanted to order food so we left and walked to Miller's Ale House. We are platinum with a major Hotel brand but booked this trip last minute and won't make the mistake again." [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Sonesta Essential Orlando Airport](https://images.trvl-media.com/lodging/1000000/460000/455400/455359/fb8c35c6_y.jpg) ### Sonesta Essential Orlando Airport 8/10 Good "Took the shower water forever to get warm. The bathroom sink pressure was very low. Other than that experience was nice " [](https://expedia.ca/Orlando-Hotels-Sonesta-Essential-Orlando.h455359.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 8/10 Good "Great!" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ## Find out more about Winter Park ## Winter Park Cottages information | Number of reviews | 90 | | ----------------- | ------------ | | Accommodation | 260 Cottages | | Lowest Price | CA $198 | | Highest Price | CA $1,218 | ## Frequently asked questions ### How much do cottages in Winter Park cost? ### Why book your cottage in Winter Park with Expedia? ### How can I find cheap cottages in Winter Park? ### What is there to do in Winter Park near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hyatt Hotels in Aloma ](https://www.expedia.ca/Aloma-Orlando-Hotels-Hyatt-Hotels.0-n553248635975863638-0--bHyattHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Aloma ](https://www.expedia.ca/Aloma-Orlando-Hotels-Spa-Hotel.0-n553248635975863638-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Aloma Hotels ](https://www.expedia.ca/Aloma-Orlando-Hotels.0-n553248635975863638-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Altamonte Springs ](https://www.expedia.ca/Altamonte-Springs-Apart-Hotels.d5965-aaApartHotels.Travel-Guide-Accommodation) - [Guest Houses in Altamonte Springs ](https://www.expedia.ca/Altamonte-Springs-Guest-Houses.d5965-aaGuestHouses.Travel-Guide-Accommodation) - [Resorts in Altamonte Springs ](https://www.expedia.ca/Altamonte-Springs-Resort-Hotels.d5965-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Altamonte Springs ](https://www.expedia.ca/Altamonte-Springs-Townhomes.d5965-aaTownhomes.Travel-Guide-Accommodation) - [Inns in Cape Canaveral ](https://www.expedia.ca/Cape-Canaveral-Inns.d6484-aaInns.Travel-Guide-Accommodation) - [Lodges in Cape Canaveral ](https://www.expedia.ca/Cape-Canaveral-Lodges.d6484-aaLodges.Travel-Guide-Accommodation) - [Ranches in Cape Canaveral ](https://www.expedia.ca/Cape-Canaveral-Ranches.d6484-aaRanches.Travel-Guide-Accommodation) - [Hotels near Casa Feliz Historic Home Museum ](https://www.expedia.ca/Casa-Feliz-Historic-Home-Museum-Hotels.0-l6154784-0.Travel-Guide-Filter-Hotels) - [Hotels near Crealde School of Art ](https://www.expedia.ca/Crealde-School-Of-Art-Hotels.0-l6239848-0.Travel-Guide-Filter-Hotels) - [Motels in Eatonville ](https://www.expedia.ca/Eatonville-Motels.d12161-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Fern Park ](https://www.expedia.ca/Fern-Park-Apart-Hotels.d7377-aaApartHotels.Travel-Guide-Accommodation) - [Holiday Park Resorts in Fern Park ](https://www.expedia.ca/Fern-Park-Holiday-Parks.d7377-aaHolidayParks.Travel-Guide-Accommodation) - [Houseboats in Fern Park ](https://www.expedia.ca/Fern-Park-Houseboats.d7377-aaHouseboats.Travel-Guide-Accommodation) - [Inns in Fern Park ](https://www.expedia.ca/Fern-Park-Inns.d7377-aaInns.Travel-Guide-Accommodation) - [Resorts in Fern Park ](https://www.expedia.ca/Fern-Park-Resort-Hotels.d7377-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Fern Park ](https://www.expedia.ca/Fern-Park-Townhomes.d7377-aaTownhomes.Travel-Guide-Accommodation) - [Pensions in Florida ](https://www.expedia.ca/Florida-Pensions.d211-aaPensions.Travel-Guide-Accommodation) - [Pousadas in Florida ](https://www.expedia.ca/Florida-Pousadas.d211-aaPousadas.Travel-Guide-Accommodation) - [Hotels near Full Sail University ](https://www.expedia.ca/Full-Sail-University-Hotels.0-l6154770-0.Travel-Guide-Filter-Hotels) - [Hotels near Harry P. 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